m-Chloroperbenzoic acid → 2-(6-Isoamylsulfinyl-2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 499408Notes

Reaction equation

HRID 499408 reaction equation
[CH2:1]([S:6][C:7]1[N:12]=[C:11]([C:13]2[S:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17](=[O:19])[N:18]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)(Cl)Cl>[CH2:1]([S:6]([C:7]1[N:12]=[C:11]([C:13]2[S:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17](=[O:19])[N:18]=2)[CH:10]=[CH:9][CH:8]=1)=[O:32])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 229395222-[6-(Isoamylthio)-2-pyridyl]-4H-1,3-benzothiazine-4-one

Product 1

HCID 597504792-(6-Isoamylsulfinyl-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-[6-(Isoamylthio)-2-pyridyl]-4H-1,3-benzothiazine-4-one (0.15 g, 0.44 mmol) was dissolved in chloroform (50 ml), and a solution of 3-chloroperbenzoic acid (ca. 77%, 0.10 g, 0.46 mmol) in chloroform (10 ml) was added dropwise thereto. The reaction mixture was stirred at room temperature for 1 hr. The solvent was evaporated, and the residue was recrystallized from hexane-ethyl acetate to give the titled compound (0.15 g, 96%) as pale yellow amorphous.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a9f86d9480af4c66a8d3a514db3870e5
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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